Ch. 01: Several Firsts with a Friend - Sex Stories

Ch. 01: Several Firsts with a Friend

... myself a little bit faster. A slight squeak came out between her lips. I leaned in and pressed my lips, splitting hers and slipping my tongue in as I began to actually fuck the sweet cougar beneath me. Her leg flailed upward to give me the leverage needed to delve deeper.

I looked down at the sight below me and she upward. Our eyes met again and unspoken words were communicated. Thrusting and pumping I continued to press hoping no one approached on the path or looked out the nearby windows, to interrupt our pleasure. Her hands were on my back and I felt the sensations begin to overwhelm me. My balls slapped against her ass all the while becoming a a pair of boiling cauldrons.

"Im going to cum," I said. Her voiced softly whispered her gentle response, "yeah?"

"Mmhmm," was all the response I managed at first. "Where should I do it?" I nervously asked. Confidently and knowingly she told me, "inside me."

I responded, "are you su..." it's a good thing she gave me a feverish nod as she said, "oh yes," and her legs wrapped around my waist and back to pull me in, because I didn't even get the question out as I boiled over and began to explode, still thrusting as I filled her wet milf pussy with my young seed. Bolt after bolt fired out and my cock pulsed until my full load was deposited within her womb. I pressed to the hilt to push it all in and savor the sensation. We kissed and laughed together. It had finally happened and in our own unique way, with our own unique ...

... connection. I sat only for a moment as we caught our breath, having finally consummated our special friendship properly.

Finally we untangled our body's and got our clothes which were only half off back on. The back of her T-shirt was covered in dry leaves and a light dusting of dirt. She assured me it wouldn't be an issue.

We decided to finish walking and talked for almost another hour in those woods encountering a pair of strangers walking toward our "secret" spot. This was just moments after we'd left it and we pressed on along the trail for a good while after the encounter and before returning to the car. I drove her back to where I'd picked her up and I dropped her off. I felt amazing and over the moon about what had happened but felt bad because I wasn't sure she had orgasmed (years of experience later, I know she didn't but I suspect she did finish the deed on her own to better effect then normal).

The next day she called me to tell me how wonderful it was. She said the feeling of sneaking in, dirt covering the back of her shirt and ass, with cum dripping into her panties had drove her wild. She asked when we could do it again and I eagerly replied that I wanted to as soon as possible. She explained that she wanted our next shared experience to be special, comfortable, and not so rushed. She wanted to get a nice hotel room and spend real time together. Over the next few days we picked a date, hotel and talked fantasies. When the date came, I was told a time and ...